Open AccessTopological Control of Columnar Stacking Made of Liquid‐Crystalline Thiophene‐Fused Metallonaphthalocyanines
Author(s) -
Suzuki Hiroyuki,
Kawano Koki,
Ohta Kazuchika,
Shimizu Yo,
Kobayashi Nagao,
Kimura Mutsumi
Publication year - 2016
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201500205
Subject(s) - stacking , thiophene , intermolecular force , columnar phase , materials science , liquid crystal , liquid crystalline , crystallography , phase (matter) , side chain , chemical physics , molecule , nanotechnology , polymer , chemistry , optoelectronics , organic chemistry , composite material
The spontaneous organization of two‐dimensional polyaromatic molecules into well‐defined nanostructures through noncovalent interactions is important in the development of organic‐based electronic and optoelectronic devices. Two regioisomers of thiophene‐fused zinc naphthalocyanines ZnTNc endo and ZnTNc exo have been designed and synthesized to obtain photo‐ and electroactive liquid crystalline materials. Both compounds exhibited liquid crystalline behavior over a wide temperature range through intermolecular π–π interactions and local phase segregation between the aromatic cores and peripheral side chains. The structural differences between ZnTNc endo and ZnTNc exo affected the stacking mode in self‐assembled columns, as well as symmetry of the two‐dimensional rectangular columnar lattice. The columnar structure in liquid crystalline phase exhibited an ambipolar charge‐transport behavior.